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Thanks to loopholes, workarounds and momentous court rulings, outside money is playing a bigger role than ever

U.S. elections are increasingly being shaped by the hundreds of millions of dollars being poured into campaigns by outside donors. Using FEC filings and FEC data collected by the Center for Responsive Politics, Al Jazeera examined the interests, strategy and agenda of ten major individual donors and two groups. The numbers aren't necessarily comprehensive, however, as election law now allows donors to anonymously fund so-called "dark money", or 501(c)(4) groups.

Former hedge fund manager Tom Steyer, who made his billions in large part by investing in planet-polluting energy companies, has in the last few years become perhaps the most active, aggressive and generous environmental activist in America. Through his PAC, NextGen Climate, he's pledged $100 million to candidates in federal races in the current election cycle, has invested heavily in a handful of California races, and has run TV ads attacking Republican Florida Gov. Rick Scott whose Democratic challenger is the more eco-friendly Charlie Crist.

"He's a latter-day born-again environmentalist," said Dave Levinthal, a senior reporter for the Center for Public Integrity. "He's turning into one of the pre-eminent big money sugar daddies for Democrats in 2014 with no signs of ratcheting back for 2016 either. He cares about three issues — the environment, the environment and the environment."

Foes on the right, however, accuse the 57-year-old of embracing the green movement to further his own financial interests. Typical of such attacks, John Hinderaker of Powerlineblog.com wrote in April that Steyer "depends on government connections to produce subsidies and mandates that make his 'green' energy investments profitable."

Democrats don't seem to mind, grateful to have a gigantic donor to counter the money of figures like Sheldon Adelson and the Koch brothers on the Republican side.

Levinthal exaggerates a little bit on the singularity of Steyer's environmental focus. In 2012, he also dropped almost $22 million on Proposition 39, a successful voter referendum in his home state of California that closed a loophole that helped multi-state corporations avoid paying Golden State taxes.

Unlike some of the other big-name donors like Adelson and Foster Friess, Steyer is seen as being smart and strategic with his giving. "Instead of the 'I-know-best' mindset that a lot of these big donors have, my impression is he is a real student of this stuff and he has a higher level of aptitude," said Politico senior writer Ken Vogel, author of "Big Money," a story of campaign donors in the 2012 election cycle. "He is not going to be signing off on foolhardy gambits."

That said, Steyer also isn't playing it safe. Rather, he's been getting involved in several coin-flip-close contests, from the Scott-Crist battle in Florida, to tight Senate races in Iowa, New Hampshire and Colorado. "It's a very aggressive play he's making here," Levinthal said. "There's high risk, high reward here. Those are all competitive races. He could be 4-0 or 0-4. Either would make sense."

While Steyer isn't quite a household name yet, Republicans hope to turn him into one. Last month, American Crossroads began airing ads in Iowa tying Steyer's support for Democratic Senate candidate Bruce Braley to his opposition to the Keystone XL pipeline. And the Republican Governors Association earlier this year went live with MeetTomSteyer.com, a website devoted to attacking him.

Spending heavily to back Democrats may just be the warm up: Steyer has hinted that he may be interested in running for Senate in California in 2018 if Sen. Dianne Feinstein, now 81, retires.

American Crossroads, the Super PAC founded in 2010 and operated by former George W. Bush campaign wizard Karl Rove, came to its own crossroads after the 2012 election, in which the group and its affiliates spent more than $175 million on losing candidates in more than two-dozen federal elections. They also spent a further $100 million in support for Republican presidential nominee Mitt Romney.

Despite that washout, Rove still managed to raise more than $100 million to spend in the 2014 midterm elections,on a GOP slate largely favored by Crossroads. Should the GOP take over the Senate, Rove will claim bragging rights to boost his coffers for 2016.

Still, the struggles of Crossroads represent the ongoing schism within the GOP between establishment Republicans and Tea Party followers suspicious of incumbents and frustrated by mainline Republican government spending and interventionist foreign policies. Rove personifies the Bush era, which the Tea Party rebelled against as insufficiently fiscally responsible.

The sources of Crossroads' funding remain murky, because the Supreme Court's 2010 Citizens United ruling allows for donors to remain anonymous. But the candidates it backs tend to be considered more mainstream conservative, supporters of tax cuts and the deployment of the U.S. military abroad.

The group's current slate of ads raise several other issues du jour, attacking Sen. Jeanne Shaheen in New Hampshire for voting for the Affordable Care Act, Independent candidate Greg Orman in Kansas for supporting "amnesty" for undocumented immigrants and "liberal gun control," and Democratic Senate candidate Bruce Braley in Iowa for "giving lawbreakers food stamps and Medicare." Crossroads actually spent $100,000 in 2013 to run ads supporting a Senate immigration reform package that included a path to citizenship for undocumented immigrants -- a provision they now appear to oppose as "amnesty."

After Senate seats in Indiana and Missouri slipped from the GOP's grasp in the 2012 election because of comments by their candidates that were offensive to women, Rove and his supporters blamed their Tea Party backers, drawing fire from Sen. Ted Cruz of Texas and former Alaska Gov. Sarah Palin.

"Crossroads represents something approaching a face of the Republican Party that's less confrontational and abrasive", said David Schultz, election law professor at University of Minnesota. "They got smarter in terms of finding candidates this year who are not as gaffe-prone."

At least in the primaries, time around, most of the GOP establishment candidates won. In the tensest standoff, Sen. Thad Cochran survived a primary fight with State Sen. Chris McDaniel. Crossroads supported Cochran in the primary and then also gave $50,000 to Mississippi Conservatives, a pro-Cochran PAC, days before the June 24 runoff. At the time, the Washington Post quoted Crossroads spokesman Paul Lindsay claiming Crossroads would not get involved in the runoff.

The Service Employees International Union (SEIU) is rare among America's labor unions not only because of its independence from the AFL-CIO, but also because its membership and political influence are growing.

The union's 527 has spent nearly $10 million to help elect Democrats and promote union-related ballot measures in the current election cycle.

"They're very involved not only when it relates to labor law changes but a broad swath of issues that are important," said David Schultz, who teaches election law at the University of Minnesota. "SEIU is out there supporting raising the minimum wage, for instance. They support candidates whose views they like on issues of affordable health care, changes in collective bargaining laws, pushing to have people they like appointed to the National Labor Relations Board or OSHA [the Occupational Safety and Health Administration]".

After spending $66 million in 2008 to help elect President Barack Obama, top SEIU officials were reportedly frequent visitors to 1600 Pennsylvania Avenue. Obama appointed several SEIU figures to significant roles, including one controversial 2010 recess appointment struck down by the Supreme Court.

SEIU influence isn't derived only from cash contributions: In Texas, Florida, Nevada, Arizona and elsewhere, it has supplied an activist core of campaign workers, and a reliably raucous crowd at rallies of favored candidates. SEIU members flanked Senate Majority Leader Harry Reid when he met the press after surviving a tough re-election challenge in 2010.

The union, whose 1.8 million members work in more than 100 professions, is strongest in health care, hospitality and public services. And it has lately taken a lead in efforts to unionize fast-food chain restaurants.

SEIU political spending has a mixed record of success: It reportedly spent $2 million on the failed effort to recall Wisconsin Gov. Scott Walker over the curbing of public-sector union rights. The union also spent more than $10 million in 2013 on TV ads supporting a comprehensive immigration reform bill that was passed by the Senate but ignored by the House of Representatives.

Since the end of his three-term-run as mayor of New York City, Michael Bloomberg has had a singular focus: Getting Congress and state legislatures to pass stricter gun laws.

A media magnate with a net worth of more than $30 billion, Bloomberg pledged earlier this year to spend $50 million on pro-gun-control candidates, and his new group, Everytown for Gun Safety, has started rating lawmakers on their stands on gun-related measures. When he gives to individual candidates, they are usually Democrats, although his Independence USA PAC insists it has a "long history of supporting candidates and referenda that reflect his independent and non-partisan approach to government."

It's not that Bloomberg's interest in gun control is new; he's simply narrowed his political activity to focus on that one matter. While in office, he and Boston Mayor Tom Menino founded Mayors Against Illegal Guns, a bipartisan coalition of more than 1,000 mayors that is now also the parent group to Everytown for Gun Safety.

Bloomberg, 72, is unique among the megadonors on the American political scene for having run for and served in political office. For that reason, it surprises some observers that he so blatantly inserts himself in some races where his overt involvement can be used to tar the very candidate he's supporting.

"He may think that putting his face out there is helping his causes, but that can also backfire," said David Schultz, political science professor at Hamline University and election law professor at University of Minnesota. "People might associate what might be some very good ideas with a caricature. Personality can be as powerful drawing factor but also a powerful force to rally people."

Foes of gun control – most notably the National Rifle Association – have pounced. In August, the NRA announced a multimillion-dollar ad campaign focused on attacking Bloomberg as a "billionaire-elitist-hypocrite."

Bloomberg has been cautious in certain cases. After threatening to back primary challenges to Sen. Mark Pryor of Arkansas and Sen. Kay Hagan of North Carolina, he backed down, said Ken Vogel, a POLITICO senior writer and author of "Big Money," a book about campaign finance in the 2012 election.

"Democrats were really freaked out, so he backed off," Vogel said. "He realized, 'If I ... primary them, what's going to happen if I win?' His candidate would've been creamed in the general election."

So far, Bloomberg's anti-gun largesse hasn't produced much in the way of policy shifts or legislative success. After a rush of interest following the mass shooting at Sandy Hook Elementary School in Connecticut, the issue has again receded and few candidates are talking about it this fall. Still, Bloomberg can afford to be patient.

"He knows this is a cyclical issue," Dave Levinthal, senior reporter at the Center for Public Integrity. "We will be talking about gun rights again in a major way at some point in the future."

Billionaire financier George Soros was a prime target of Republican attack ads a decade ago. Democratic candidates tied to or funded by him were targeted as bought-and-paid-for by a shadowy Hungarian immigrant who said that defeating President George W. Bush was the "central focus of my life."

But Soros appears to have fallen off the radar of GOP campaign ad-makers these days, perhaps because they have bogeymen with far better name recognition, such as President Barack Obama himself, to aim at.

Soros, however, hasn't gone away. The 81-year-old ponied up $1 million to the liberal American Bridge 21st Century PAC; has maxed out his contributions to dozens of Democratic House and Senate candidates; and has even gotten a head start on 2016 with a $25,000 gift to Ready for Hillary.

Besides the general slate of Democratic causes, Soros' primary issue these days may seem an ironic one – campaign finance reform. While he was among the earliest big spenders, dumping $25.5 million in the 2004 cycle on groups such as MoveOn.org, America Coming Together, and the Center for American Progress, he has been an outspoken critic of the Supreme Court's Citizens United ruling that opened the door to a new order of megadonors.

"There is no way those concerned with the public interest can compete with" the new breed of big donors able to give in secret, Soros spokesman Michael Vachon said in 2012. "Soros has always focused his political giving on grass-roots organizing and holding conservatives accountable for the flawed policies they promote."

Soros' 2004 spending failed to help unseat Bush, and he subsequently co-founded the Democracy Alliance, which he allowed to direct his political largesse.

One of Soros' biggest political successes, however, has been in funding a set of think tanks and organizations that counter the network of similar groups on the right. The conservative groups, like the Heritage Foundation, have been providing intellectual ammunition for Republican candidates and activists for decades. Among Soros' beneficiaries are the Center for American Progress and the Brennan Center For Justice.

"His strategy has proven quite effective," said Andy Kroll, who covers campaign finance for Mother Jones magazine. "Look at what the Democracy Alliance has achieved" in getting Democrats elected in 2008 and 2012."

Soros also seems happier being less visible, and so, less prone to being painted by the likes of Fox news as a billionaire puppet master orchestrating a worldwide conspiracy to undermine America. When Soros gave $1 million to a pro-Obama super PAC in September 2012, it made some news, but was hardly eye-popping compared to what the Koch brothers, Sheldon Adelson and Tom Steyer had dropped into the race for the presidency.

"Soros, while not completely disappearing from the political realm, seems to have focused his energy and resources on the more permanent politics on the left side of the aisle," Kroll said. "It's not as headline grabbing, but it's arguably also more effective."

Bloomberg/Getty Images

A family as wealthy and vast as the Waltons, owners of Walmart, is difficult to pin down ideologically. While the lion's share of their political giving goes to conservative issues, some Democrats also benefit from the more idiosyncratic largesse of some of Sam Walton's heirs.

The family's staggering wealth – six members combine for more than $120 billion in net worth – makes their giving potentially influential, but for the most part it is motivated by predictable business interests such as low taxes, anti-union laws and preventing hikes in the federal minimum wage.

The company insists the family plays both sides. In 2013, a Walmart spokeswoman told the Huffington Post that Democrats enjoyed 49 percent of giving in the 2011-2012 cycle.

"They have interests in agriculture, health care insurance, minimum wage laws, occupational safety regulations, and they're clearly looking at how specific federal regulations affect their businesses," said David Schultz, election law professor at University of Minnesota. "The older generation seems to be in in lockstep, but clearly as we get beyond the original founder of Walmart and his children, we're starting to see a splitting off of those interests. But so far, we still see more similarities than parting."

A central focus of Walton giving in recent years has been opposition to the Affordable Care Act (ACA). Yet since Obamacare went into effect, the company hasn't made much noise and experts believe they have moved on to other concerns.

Analysis of Walmart giving also reveals a pattern of support for gun rights and candidates endorsed by the National Rifle Association. Walmart is the largest retailer of firearms in America.

Still, younger Walton kin appear to be branching out, said Jay Barth, political science professor at Hendrix College in Conway, Ark. As an example, Barth pointed to Alice Walton's donations to both the Texas gubernatorial campaign of Republican Greg Abbott as well as one to Ready For Hillary.

In addition, Barth noted that the company also promotes political aims through the Walton Family Foundation, which has donated big bucks to pay for buildings then donated to charter schools. The Foundation also give copiously to environmental groups — the Conservation International Foundation and the Environmental Defense Fund each receive more than $10 million a year.

Walmart also spends more than $6 million a year on federal lobbyists. In an effort to defuse some of its more vociferous critics, in May 2012, the company dropped its longtime membership in the American Legislative Exchange Council, a conservative consortium that backed Arizona's controversial anti-immigration law and pushes for tough, restrictive voter ID laws.

"You can't paint the family with a single brush," Barth said. "We are starting to see more diversity in younger generations who are now becoming politically active. We see the corporation becoming more progressive environmentally and on discrimination issues than a generation ago, too."

Charles and David Koch, the Wichita, Kansas brothers whose combined wealth totals more than $75 billion emerged in the political spotlight before the last midterm cycle, when their financial support helped launch the tea party movement and funded successful primary challenges to several incumbent Republicans. But the tea party was only the latest manifestation of the Kochs' longstanding dissatisfaction with the GOP establishment, which during the Bush administration had increased government spending and debt while engaging in open-ended wars overseas.

As libertarians – in fact, David Koch was the vice presidential candidate on the Libertarian Party ticket in 1980 – the brothers believe limited government, free market economics and fiscal conservatism. Long before they raised or gave $400 million in the past two election cycles, the Kochs spent decades funding think tanks whose research provides intellectual ammunition for conservative causes. Their foundation also provides grants to more than 250 U.S. colleges to pursue studies related to libertarian philosophy. Americans For Prosperity, another Koch entity, was active in fighting the Affordable Care Act.

"It really came to a head in the Bush administration when they had a Republican White House and Republicans controlled both chambers of Congress and yet they saw the Republicans embodying the big-government reckless spending they abhor," said Ken Vogel, author of Big Money, which focuses on the Kochs' activities.

The Koch project, via the tea party and other initiatives, aims to shift the fundamental values of the GOP. While they failed to affect the outcome of the 2012 election, the Kochs' influence was evident in subsequent standoffs between the House of Representatives and President Obama over debt and budget issues, in which the GOP congressional leadership was more responsive than in the past to anti-spending sentiment in their own ranks.

Democrats have taken the Kochs' growing influence as an opportunity, make it the focal point of political attacks. Senate Majority Leader Harry Reid called them "un-American" in a Senate speech, and TV ads across the nation show grainy photos of the men hovering over whichever local Republican candidate they support.

There is some evidence that the Kochs are concerned that their political activism could have negative consequences for their business interests. Koch Industries is a sprawling $115 billion empire that produces a litany of popular and common household items from Quilted Northern toilet paper to Stainmaster carpeting. To counter any negative publicity, the company has aired TV ads touting its contributions to the economy.

"They've been insulated because most of their consumer products don't have their name on them and people don't realize they are profiting when they buy Brawny paper towels or Dixie Cups," Vogel said. "They've got to get a whole lot more famous than they are and a whole lot more despised than that before it starts hurting their bottom line."

Charles Koch

Wichita Eagle/Getty Images

David Koch

Paul Zimmerman/Getty Images

It is unclear, even now, just how much money Las Vegas Sands CEO Sheldon Adelson and his wife, Miriam, spent on political efforts in the 2012 election cycle. Reports and studies have set the figure at $54 million, $93 million and even north of $150 million – and he's not telling.

What is clear, however, is that the vast sum bought the casino magnate little more than a place in the national consciousness as a major-league Republican campaign contributor. And while that reality has not daunted Adelson going into the 2014 and 2016 cycles, it reflects an unsystematic, gut-level style of giving bereft of input from advisors that could maximize his impact. In 2012, he most notably plunged $15 million into the Restore Our Future PAC, which supported former House Speaker Newt Gingrich, but also Mitt Romney and a litany of Republican candidates for Senate and Congress. Out of all that, his sole notable triumph – and his money can hardly be seen as a deciding factor – was the election of Dean Heller to the Senate from Nevada.

"He backed Newt Gingrich because it's like, 'Newt and I go back. Newt's a friend of Israel. Newt's a smart guy. I like Newt,' " said Eric Herzik, political science professor at University of Nevada at Reno. "His giving is very much on a personal basis, and when Gingrich loses, 'You don't see Adelson saying, 'Oh, he stole my money.' He says, 'So be it.' "

Just because Adelson's giving is lavish and idiosyncratic doesn't mean he spends without purpose. Unwavering support for Israel is the closest thing the 81-year-old son of a Boston cab driver has to a litmus test for giving, and his contributions in 2014 show it: Adelson's donating big not just to Republican groups and the obvious GOP Senate candidates, but also to Jewish candidates like Elan Carr, an Iraq War vet running for Congress in the L.A. area. As the self-described wealthiest Jewish person in the world, his $37 billion net worth funds a litany of political, cultural and social projects in Israel. One, Birthright Israel, has paid for free trips to the country by thousands of young Jewish Americans, trips designed to impart on the kids the importance of continued American support there.

Adelson's other key political driver is an anti-union zeal that dates to his earliest tussles with the Service Employee International Union when he opened the Venetian Hotel-Casino in Las Vegas in 1998. He refused to allow the hotel employees to unionize, leading to years of protests and litigation. More recently, he has been outspoken against Internet gambling, setting him at odds with other casino owners and, for a time, the American Gaming Association, which has since opted to be neutral on the issue largely out of deference to him. Yet he funds many candidates – including Heller – who support it, so it's hardly a defining matter.

More than anything, Adelson is a headstrong, consummate businessman who followed his instincts even as conventional wisdom suggested he was wrong or nuts or both. Many doubted Las Vegas would become a business convention destination or that the Macau gambling market could handle the enormous influx of casino space he built, but both gambits helped make him super-rich.

The problem is, politics isn't business, says Ken Vogel, a POLITICO senior writer and author of "Big Money," a book about the spending in the 2012 election cycle.

"He's a great case study in this flawed thinking these donors have," Vogel said. "They've been so successful in business, in bucking conventional wisdom. So when people tell him he's doing this wrong, he's thinking to himself, 'I know best. I think everyone else is wrong and my gut is right.' And it turns out, his gut doesn't help him in politics."

Roslan Rahman/Getty Images

Rex Sinquefield is something of a mystery to those who study money in politics. In his home state of Missouri, however, he has no name-recognition problem; on the contrary, Democratic and progressive groups are making his name a central feature of attacks on local Republicans.

Sinquefield, 70, is a St. Louis native who lived for a time in an orphanage because his parents couldn't afford to care for him, and once considered becoming a Catholic priest. Instead, he studied economics at the University of Chicago and became rich as a stock index-fund investor.

Since retiring, he has pumped huge sums of money into Missouri politics with a focus on eliminating the state's income tax and on promoting charter schools. The St. Louis Beacon estimates that Sinquefield has spent $28 million between 2008 and 2013 on state politics, and that doesn't include the Show-Me Institute, a conservative think-tank he funds to the tune of about $1.4 million a year.

In the 2014 cycle, Sinquefield has thus far poured more than $3 million into state races. No single donor has ever spent anything close to that. He also gives in federal races, mostly through established pro-GOP PACs, but the national level is not where his focus lies.

"I don't know that we know the full extent of his participation nationally because of the dark money rules, but in Missouri, he is clearly the biggest campaign money guy to come along," said former Associated Press reporter Scott Charton, whose spent more than a decade covering the Show-Me State's politics.

In support of his passion for cutting taxes, Sinquefield has brought in Texas Gov. Rick Perry to headline Missouri fundraisers, and, for a long time, cited Kansas Gov. Sam Brownback's success in drastically lowering taxes in the neighboring state.

Sinquefield's spending may be extensive, but its impact has been limited. In 2013, he spent big to persuade the legislature to support a huge income tax cut that was then vetoed by Democratic Gov. Jay Nixon. Four Republican state lawmakers who voted to sustain the veto were targeted by Sinquefield in primaries this year – and all four survived.

"He has an army of lobbyists," Charton said. "The joke around here is that they're working very hard to turn a billionaire into a millionaire."

Sinquefield was the target of a storm of negative publicity in September, most notably the controversy that erupted late in September over reports of a ham-handed attempt to solicit local reporters to anonymously write blog posts for a political organization he had funded.

"His groups have shown they're willing to blow his money like mad," Charton said. "That's what's creating anxiety here. He may not win today or tomorrow, but if he's willing to sustain these campaigns for years, eventually he could have some success."

The least overtly partisan of the big-hitter donors these days may be Google executive chairman Eric Schmidt. That may reflect a political agenda aligned with the company he led for a decade, promoting policies related to information technologies, low taxes and immigration reform.

"You don't hear him spout off about gun rights or abortion or fire up a different kind of constituency," said Dave Levinthal, senior writer for the Center for Public Integrity. "Eric Schmidt's political participation isn't for some personal ideological reason. Primarily, it's not about his own political leanings. He's there to be a public representative for Google, which is a lot different than some other big-time political money players who are very animated by a particular pet issue."

It wasn't always thus. Schmidt – and Google – started out focused on supporting Democratic candidates, and was an outspoken supporter of and advisor to President Barack Obama going back to 2008. He has helped persuade the president to include an increase in the number of high-skilled workers companies like Google can hire from foreign countries in the push for comprehensive immigration reform.

Both the 59-year-old Schmidt, whose net worth is estimated at $9.4 billion, and Google have become decidedly more bipartisan in recent years, most notably by hiring former Republican Rep. Susan Molinari as the company's chief Washington D.C. lobbyist, and giving more than $700,000 to tech industry-friendly Republicans in the 2012 cycle . Among Republicans Schmidt has personally maxed out donations for this year are House Majority Leader Kevin McCarthy of California and House Judiciary Committee chairman Bob Goodlatte of Virginia.

"He used to support only Democrats, but in recent years, he's been giving more to Republicans, like [South Carolina Sen.] Lindsay Graham, who is pro-immigration reform," said Michelle Quinn, a technology and politics columnist for the San Jose Mercury-News. "He's given evenly to the Democratic and Republican Senatorial Campaign Committees in the current cycle. He's still playing it pretty close."

In recent years, as Google has delved into new businesses, Schmidt has gone to work supporting candidates and office-holders on the state and federal level whose views favor deregulation of the telecommunications industry and the promotion of autonomous vehicle technology. He's also a well-known advocate of Net neutrality, fearful that Internet service providers will disrupt the free-flowing nature of the Web.

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Marriage equality may now exist in more than half the states, and more court victories for same-sex unions seem to come almost daily, but Quark founder Tim Gill is not ready to reduce or redirect his political giving. The 60-year-old Colorado philanthropist is now turning his attentions toward other line-items on the gay-rights agenda – most notably, employment and housing discrimination protections.

Gill, whose net worth is estimated to be more than $400 million and who estimates he's given about $300 million to gay causes over the past quarter-century, is a pioneer in campaign donations tied to support of the rights of gays, lesbians, bisexuals and transgender people. He tiptoed into the game in 2000, spending a mere $300,000; by 2006, he was behind more than $15 million and had founded Gill Action Network to coordinate pro-gay rights donors.

Gill's efforts have been most pronounced on the state level, which is why he doesn't rate among the top federal givers even as Time Magazine heralds him as "The gay mogul changing U.S. politics." Earlier this year, he announced he'd spend $25 million over the coming five years promoting gay rights in states like Missouri and Texas,. His efforts in his home state – once reliably red; now considered a swing state with Democrats in control of the state legislature – are seen as a model.

"We can't allow two distinct gay Americas to exist," Gill told the New York Times in April. "Everybody should have the same rights and protections regardless of where they were born and where they live."

While most of Gill's personal giving has gone to Democratic candidates, he is keenly aware of the need to persuade Republican leaders to support gay equality. To wit, Gill Action has had two Republican executive directors, Kirk Fordham and Patrick Guerriero, in its eight-year history.

"Tim Gill believes you're going to do better if you make sure you have the expertise of people who can cross party lines and talk to everyone," said Bob Witeck, a publicist who counsels major brands including Marriott and American Airlines on appealing to LGBT consumers. "The thing I'm impressed by is that his business background makes him very interested in results. He's very much interested in knowing what the needle looks like and how to push the needle."

Gill Action is best known for its "punish the wicked" approach, as Fordham recently called it. In New York, for instance, the PAC struck back at three state senators – including two Democrats – for opposition to same-sex marriage, working to replace them with pro-equality senators in 2010.

"Tim Gill was the first major gay-rights donor," said Ken Vogel, author of "Big Money," a book about the major campaign donors of the 2012 cycle. "Now there are quite a few, but when he started out that was kind of a niche. Obviously, it's been quite effective in getting the Democratic Party to really embrace a more aggressive stance on this issue."

The 2012 election cycle saw Wyoming-based investment manager Foster Friess emerge as a colorful new face among conservative big-money donors. Friess, 74, is most notable for spending $2 million through his Red, White and Blue Fund in support of the failed presidential bid of Rick Santorum, keeping the former senator from Pennsylvania in the race months longer than expected.

"He's proof that a big-dollar donor can have a singular effect on national politics," said Dave Levinthal, senior reporter for the Center for Public Integrity.

Friess wasn't new to Republican politics, but most of his prior donations were more conventional gifts to such entities as the Republican Governors Association and the Koch brothers' PAC. In 2011, he also put up $100,000 to help Wisconsin Gov. Scott Walker beat back a recall effort, reflecting an anti-union stance.

He's given more modestly in the current cycle so far, at least via Super PACs and in direct donations. In many cases, he didn't give the maximum $2,600 to Republican candidates he likes, unusual for a donor of his reputation.

Friess is known as a staunch Christian conservative, and his giving is animated by socially conservative candidates — such as Santorum — who oppose abortion and gay rights. His Super PAC's website reflects his views, listing five tenets, including the belief in "American exceptionalism" and the idea that "the family is the foundation for a healthy society and strong economy."

Friess rejected the criticism from fellow Republicans that his support of Santorum kept the primary season going and harmed the party's eventual nominee, Mitt Romney.

"It was absolutely worth it because I allowed Rick Santorum to express views and ideas that the American people wanted to hear and needed to hear that never would have been articulated," Friess said in 2013.

Friess did cause some headaches for Santorum, most notably by expressing an outlandish approach to contraception in an MSNBC interview in April 2012.

Still, he has said, he enjoyed his moment in the spotlight alongside Santorum. He rode the candidate's campaign bus, appeared at rallies and treated the experience like "political fantasy camp," said Ken Vogel, author of the book "Big Money" about major donors in the 2012 campaign.

"Foster Friess loves the attention and he's really a political junkie," said Vogel said. "Others see electoral politics as a means to an end. Foster Friess loves it as a sport. He once talked about running for president himself .... After Santorum dropped out of the race, he told me, 'This was one of the greatest experiences I've ever had in American life.' "

Earlier this year, Friess told the Washington Times that he hopes Santorum will take another run at the GOP nomination in 2016. Santorum would be a long shot, he conceded, but he believes the former senator's "voice needs to be heard because our culture precedes our politics."

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